Hydroquinone → 4-(tert-Butyldimethylsiloxy)phenol

HRID 68209

Reaktionsgleichung

Reaktionsgleichung von HRID 68209
N1C=CN=C1.[C:6]1([CH:13]=[CH:12][C:10]([OH:11])=[CH:9][CH:8]=1)[OH:7].[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>CN(C)C=O.O>[Si:14]([O:7][C:6]1[CH:13]=[CH:12][C:10]([OH:11])=[CH:9][CH:8]=1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Komponenten

6

Edukt 3

HCID 785HydroquinoneHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride

Produkt 1

HCID 5973884-(tert-Butyldimethylsiloxy)phenol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2.9 parts of imidazole, 1.99 parts of hydroquinone and 3 parts of tert-butyldimethylsilyl chloride in 10 mL of dimethylformamide was stirred at room temperature for 1 hr 45 min. The reaction was monitored by TLC showed formation of product. The reaction mixture was diluted with 50 mL of deionized water and product was extracted with 2×50 mL of ether. The combined organic layer was dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography on silica gel with 5% ethyl acetate-hexanes to yield 2.24 parts 4-(tert-butyldimethylsilyloxy)phenol. NMR was used to confirm the following structure.

Aufarbeitung

  1. extractionwas extracted with 2×50 mL of ether
  2. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. custompurified by column chromatography on silica gel with 5% ethyl acetate-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-92c3430aed074b879487da802bcbe81f
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822233B2

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